- Cyanine type modified compound Intermediate and preparation method and application thereof
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The invention provides a cyanine type modified compound with the structure of the formula (I), and also provides a preparation method of the cyanine type modified compound. The Vinamidinium-salt new synthetic route is developed, the process parameters are optimized, the yield of the intermediate is improved, the product quality is also good, and the effect of increasing the yield of the next step is crucial. In addition, since the cyanine-based modified compound contains more double bonds and strong electron-withdrawing groups, it can be used as an ultraviolet - blue light absorbent.
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Paragraph 0052-0053
(2021/11/03)
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- New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential
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Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (SN2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. The evaluation of the compounds’ potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 μg mL?1
- Barbosa-Filho, José M.,Brand?o, Maria Cláudia R.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes D.,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.
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p. 1668 - 1678
(2020/10/09)
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- Synthesis, in silico Study and Antimicrobial Evaluation of New Diesters Derived from Phthaloylglycine
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New diesters derived from phthaloylglycine (7a-7i) were synthesized and their structures characterized by infrared, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The compounds were evaluated in an in silico study, which demonstrated positive features indicating a possible drug candidate. The diesters showed antifungal activity ranging from moderate to strong against strains of Candida. Compounds 7a, 7b, 7c, 7e and 7i had a moderate minimum inhibitory concentration (MIC) of 1024 μg mL?1 against all fungal strains, while 7h showed a very good MIC of 256 μg mL?1 against Candida albicans, Candida parapsilosis and Candida krusei and 64 μg mL?1 against Candida tropicalis. However, only 7h and 7i were able to inhibit bacterial growth of strains of Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa and Escherichia coli with an MIC of 1024 μg mL?1
- Alves, Francinara S.,Barbosa-Filho, José M.,Cordeiro, Laísa V.,Huang, Min-Fu N.,Lima, Edeltrudes O.,Neto, Hermes Diniz,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.,de Lima, Priscila S. V.,de Oliveira, Rafael F.,de Sousa, Abra?o P.
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p. 953 - 962
(2020/10/14)
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- Preparation method of novel thermosensitive ionic liquid and method for synthesizing chloracetate catalytically
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The invention discloses an acid functionalized-temperature controlled ternary heteropolyacid ionic liquid and a preparation method thereof, as well as an esterification method for synthesizing chloracetate catalytically. The structural formula of the heteropolyacid ionic liquid is as shown in a formula (I). The ionic liquid has a temperature responding characteristic during esterification reactionof chloroacetic acid and chloroacetic acid, is mixed with a reactant as one phase at the reaction temperature, and is further divided into two phases with the product when the temperature is reducedto a room temperature after the reaction. A catalyst and a reaction product can be separated quickly by simple filtration. The ionic liquid not only has the advantages of being convenient to recover and free of waste acid emission, but also has the characteristics of being high in esterification efficiency, good in repeated using performance and the like.
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Paragraph 0029
(2019/04/02)
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- Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions
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In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.
- Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: a) reactinghalogenated acetate with 2,4-dichlorophenolate in the presence of a phase-transfer catalyst so as to obtain 2,4-dichlorophenoxyacetate; and b) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, oil-phase halogenated acetate reacts with 2,4-dichlorophenolate under the action of the phase-transfer catalyst to prepare 2,4-dichlorophenoxyacetate, and then 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid and corresponding alcohols. Under the action of the phase-transfer catalyst, few hydrolysis by-products are produced during a reaction, fast reaction speed and high conversion rate and yield are obtained, and the amount of produced waste water is low; so industrial application of the preparation method can be easily implemented.
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Paragraph 0067; 0069
(2018/09/08)
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- Preparation method for 2,4-dichlorophenol, and preparation method for 2,4-dichlorophenolate
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The invention provides a preparation method for 2,4-dichlorophenol. The preparation method comprises the following steps: S1) mixing an initiator, phenol and a promoter in an organic solvent and carrying out chlorination under low temperature conditions to obtain the chlorination tail gas of phenol and a reaction solution, wherein the initiator is sulfuryl chloride, and the promoter is an ether compound; S2) mixing the chlorination tail gas of phenol with chlorine gas for a reaction to obtain sulfuryl chloride; and S3) mixing the sulfuryl chloride with the reaction solution and carrying out chlorination to obtain the chlorination tail gas of phenol and 2,4-dichlorophenol. Compared with the prior art, the invention has the following advantages: since chlorine gas is used as an initial chlorination raw material and continuously produces sulfuryl chloride through a reaction with sulfur dioxide in the chlorination tail gas of phenol, and then the sulfuryl chloride is continuously added into the reaction solution to obtain 2,4-dichlorophenol, so the preparation method has the advantages of high selectivity, low cost, high yield and simple flow due to adoption of continuous reaction andtail gas recycling flow; moreover, the reaction is carried out under low temperature conditions, so selectivity is improved; and the promoter is used, so a reaction rate is increased.
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Paragraph 0069; 0070
(2018/09/08)
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- A method for preparing 2, 4 - dichlorophenoxyacetic acid (by machine translation)
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The invention provides a 2, 4 - dichlorophenoxyacetic acid preparation method, comprising: A) a halogenated acetic acid with the monoester should be halogenated acetate; phenol with alkali reaction to obtain the phenoxide; B) halogenated acetate and phenol salt reaction to obtain the phenoxyacetic acid ester; C) phenoxyacetic acid ester under the effects of catalyst chloride to obtain 2, 4 - dichlorophenoxy ester; said catalyst selected from iron trichloride, aluminum trichloride, boron trifluoride, five [...], trifluoromethyl sulfonate, aluminum oxide, ferric oxide, boron trioxide, niobium pentoxide, diphenyl ether, diphenyl sulfide, benzoin two sulfide, dimethyl sulfide and dimethyl sulfide in one or several of the D) 2, 4 - dichlorophenoxy ester hydrolysis to obtain 2, 4 - dichloro acid. This invention adopts the specific reaction routes and chlorinated using a specific catalyst, good reaction selectivity, few by-products, high yield. (by machine translation)
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Paragraph 0055; 0056
(2018/09/08)
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid, belonging to the technical field of organic synthesis. The preparation method comprises the following steps: a) reactinghalogenated acetate with an anhydrous 2,4-dichlorophenolate solid so as to obtain 2,4-dichlorophenoxyacetate; and b) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, the anhydrous 2,4-dichlorophenolate solid reacts with halogenated acetate to prepare 2,4-dichlorophenoxyacetate, and then 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid and corresponding alcohols. The mass transfer effect of a solid-liquid reaction in the invention is good; few hydrolysis by-products are produced during the reaction; fast reaction speed and high conversion rate and yield are obtained; the amount of produced waste water is low; so industrial application of the preparation method can be easily implemented.
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Paragraph 0058; 0059
(2018/09/08)
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid. The preparation method comprises the following steps: A) reacting C2 or above-C2 alcohol with halogenated acetic acid soas to obtain halogenated acetate; B) reacting halogenated acetic acid with 2,4-dichlorophenolate so as to obtain 2,4-dichlorophenoxyacetate; and C) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, C2 or above-C2 alcohol reacts with halogenated acetic acid to obtain a halogenated acetate intermediate, the intermediate has good stability, few reaction by-products are produced, and high yield is realized; then the intermediate further reacts with 2,4-dichlorophenolate to obtain 2,4-dichlorophenoxyacetate; and finally, 2,4-dichlorophenoxyacetate is hydrolyzed to obtain 2,4-dichlorophenoxyacetic acid. Through a specific reaction route of the invention, the finally prepared 2,4-dichlorophenoxyacetic acid has high purity and yield, few by-products are produced, the reaction route is simple, and the application of the preparation method is facilitated.
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Paragraph 0050; 0051; 0057
(2018/09/08)
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- Preparation method for 2,4-dichlorophenoxyacetic acid
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The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid. The preparation method comprises the following steps: a) reacting haloacetic acid with 2,4-dichlorophenolate in a strong-polarity solvent so as to obtain 2,4-dichlorophenoxy acetate; and B) hydrolyzing 2,4-dichlorophenoxyacetate so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, the strong-polarity solvent is utilized, so the mass transfer effect of the reaction is improved, reaction time is reduced, the reaction is more complete, and the conversion rate and yield of the reaction are greatly improved.
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Paragraph 0038; 0039
(2018/09/29)
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- Synthesis and physico-chemical properties of ionic liquids—3-methyl-1-alkyloxycarbonylmethylpyridinium hexafluorophosphates
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Ionic liquids based on 1-alkyloxycarbonylmethyl-3-methylpyridinium and Cl– and PF6 – anions have been synthesized. The conductivity of their solutions in acetonitrile and the thermal stability over 25–500°C in air have been determined.
- Zhuravlev,Voronchikhina
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p. 940 - 944
(2017/06/28)
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- [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate, preparation method and application of [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate
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The invention belongs to the technical field of chemical synthesis, and provides [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate, a preparation method and application of [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate. The preparation method includes the steps of synthesizing chloracetate with chloroacetic acid, methyl alcohol, ethyl alcohol and n-butanol serving as the raw materials, further efficiently synthesizing chloracetate and the water phase of 2-amino-5-sulfydryl-1,3,4-thiadiazole to form (5-amino-1,3,4-thiadiazole-2-yl)ethyl thioacetate, and condensing (5-amino-1,3,4-thiadiazole-2-yl)ethyl thioacetate and aromatic aldehyde to obtain the target compound. The synthesis route is easy to operate, energy is saved, pollution is little, reaction conditions are mild, and the method is reasonable and ideal.
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Paragraph 0018; 0019; 0030; 0031
(2016/10/09)
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- Chloracetate water phase synthesis technology and novel method for preparing 2,4-D ester
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The invention discloses a chloracetate water phase synthesis technology and a novel method for preparing 2,4-D ester, and belongs to the technical field of organic synthesis. According to the chloracetate water phase synthesis technology, alcohol and chloroacetic acid are used as raw materials for preparing chloracetate in the water phase. The method for preparing 2,4-D ester comprises the following steps that (1) chloracetate is prepared; (2) 2,4-dichloroindophenol sodium is prepared; (2) the chloracetate directly takes a reaction with 2,4-dichloroindophenol sodium under the alkaline condition to obtain the corresponding 2,4-D ester. The operation of the preparation method of the chloracetate provided by the invention is performed in the water phase, so that the purity of the obtained coarse ester is higher, and can reach 99.3 percent or higher only through simple distillation; the corresponding 2,4-D ester is prepared from the chloracetate; the preparation process of the 2,4-D ester is greatly simplified; the cost is effectively reduced; the reaction time is greatly shortened; in addition, the product yield is improved; the waste water quantity is effectively reduced; the green chemical industrial requirements are met.
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Paragraph 0043; 0044
(2017/08/25)
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- METHOD OF CONVERTING ALCOHOL TO HALIDE
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The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
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Page/Page column 51; 127
(2017/01/02)
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- A lubricating oil anti-wear additive (by machine translation)
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The invention provides a lubricating oil anti-wear additive, the synthesis of a series of 2 - benzoxazole - S - carboxylic acid ester compound (Figure 1 illustrated compound) as an effective lubricating oil anti-wear additive, wherein R, R ' groups are selected from alkyl. The invention will be the same as the lubricating oil anti-wear additives used in the trimellitic acid ester (Trimellitate, TMT) this kind of lubricating oil, can be effectively controlled and reduced to such lubricating oil as the lubricating medium of the wear of the friction pair, improve the trimellitic acid ester lubricating oil effectiveness and reliability. (by machine translation)
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Paragraph 0021; 0022
(2017/06/30)
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- METHOD FOR PRODUCING CARBONATE COMPOUND AND METHOD FOR PRODUCING AROMATIC POLYCARBONATE
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The present invention relates to a method for producing a carbonate compound containing: a first step of reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (21) or a compound represented by the following Formula (22) to obtain a reaction mixture containing a carbonate compound, and a second step of bringing the reaction mixture containing a carbonate compound into contact with a strongly basic compound, in which R1 represents a monovalent organic group, and R2 represents a divalent organic group.
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Paragraph 0187-0189
(2015/06/10)
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- A simple criterion for gas chromatography/mass spectrometric analysis of thermally unstable compounds, and reassessment of the by-products of alkyl diazoacetate synthesis
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Rationale: A principal limitation of gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) is the thermal instability of analytes. We propose that the injector and column temperatures should not exceed the atmospheric pressure boiling point, without decomposition, of the highest homologue of the series being analyzed, instead of the time-consuming procedure of obtaining chromatograms using different temperatures. Methods: A series of thermally unstable diazocarbonyl compounds, alkyl diazoacetates (predicted limit of stability approx. 140 °C, the boiling point of ethyl diazoacetate), was selected for GC/MS analysis using standard equipment. Different GC separation conditions were selected so that the retention temperatures of target compounds were both below and above 140°C. Results: Analyzing alkyl diazoacetates within their thermal stability range permitted reanalysis of their typical synthesis by-products. No dialkyl fumarate or maleate impurities, principal decomposition products which have often been reported previously, were found. Instead, alkyl esters of glycolic acid nitrate, O2NOCH 2CO2R, and 'pseudo-dimeric' products, ROCO[C 2H3NO]CO2R, were discovered for the first time. Conclusions: Avoiding the decomposition of thermally unstable organic compounds during GC and/or GC/MS analysis requires estimating their degradation temperature limits. This limit can be estimated as being equal to the atmospheric pressure boiling point of the highest homologue in the homologous series under consideration that does not decompose on boiling. Copyright
- Kornilova, Tatiana A.,Ukolov, Anton I.,Kostikov, Rafael R.,Zenkevich, Igor G.
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p. 461 - 466
(2013/03/14)
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- Synthesis of 5-iodo-1,4-disubstituted-1,2,3-triazoles mediated by in situ generated copper(I) catalyst and electrophilic triiodide ion
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Mixing copper(II) perchlorate and sodium iodide solutions results in copper(I) species and the electrophilic triiodide ions, which collectively mediate the cycloaddition reaction of organic azide and terminal alkyne to afford 5-iodo-1,4-disubstituted-1,2,3-triazoles. One molar equivalent of an amine additive is required for achieving a full conversion. Excessive addition of the amine compromises the selectivity for 5-iodo-1,2,3-triazole by promoting the formation of 5-proto-1,2,3-triazole. Based on preliminary kinetic and structural evidence, a mechanistic model is formulated in which a 5-iodo-1,2,3-triazole is formed via iodination of a copper(I) triazolide intermediate by the electrophilic triiodide ions (and possibly triethyliodoammonium ions). The experimental evidence explains the higher reactivity of the in situ generated copper(I) species and triiodide ion in the formation of 5-iodo-1,2,3-triazoles than that of the pure forms of copper(I) iodide and iodine.
- Brotherton, Wendy S.,Clark, Ronald J.,Zhu, Lei
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experimental part
p. 6443 - 6455
(2012/09/21)
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- HIV INTEGRASE INHIBITORS
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Hydroxy (tetra- or hexa-)hydronaphthyridine dione compounds of Formula (I) are inhibitors of HIV integrase and inhibitors of HIV replication wherein X1, X2, R4 and R5 are defined herein. The compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
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Page/Page column 30
(2008/06/13)
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- An improved synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)
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A new and facile route for the synthesis of the novel gastrointestinal prokinetic butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (1b), which exhibited potent gastro- and colon-prokinetic activities by oral administration without significant side effects, was established. The key intermediate, butyl 4-amino-1-piperidineacetate (16), was prepared from commercially available 4-amino-1-benzylpiperidine (2) in a high yield with four steps. Compound 1b was prepared by condensation of commercially available 4-amino-5-choloro-2-methoxybenzoic acid (7) with 16 in 84% yield. This improved synthetic route was appropriate for large-scale synthesis of 1b.
- Sakaguchi, Jun,Higashi, Taijiro,Azuma, Takahiro,Suzuki, Tomio,Iwasaki, Nobuhiko,Kondo, Noriyuki,Nagata, Osamu,Kato, Hideo,Hanaoka, Miyoji
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p. 788 - 790
(2007/10/03)
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- Catalytic esterification of alcohols, carboxylic acids and transesterification reactions with cerium(IV) triflate
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Esterification reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation of (-)-menthol.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 455 - 458
(2007/10/03)
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- Carboxylic acids supported on silica: A smooth acylating agent for alcohols
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An alternative procedure for the esterification of alcohols by short-chain carboxylic acids supported on silica is presented.
- Da Graca Nascimento, Maria,Zanotto, Sandra Patricia,Scremin, Marivania,Rezende, Marcos Caroli
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p. 2715 - 2721
(2007/10/03)
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- Specific esterase activity of subtilisin toward esters of α-haloacids
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Esters of α-haloacids are specific substrates for subtilisin which catalyses their hydrolysis in aqueous media. The same esters undergo transesterifications in organic solvents in the presence of subtilisin immobilized on an alumina-phosphate complex.
- Pugniere,Juan, C. San,Previero
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p. 4883 - 4886
(2007/10/02)
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- PERFLUORINATED RESINSULFONIC ACID - A CATALYST FOR CERTAIN ORGANIC REACTIONS.
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The purpose of this work was to examine the possibility of using, as a catalyst in certain organic reactions, the perfluorinated resinsulfonic acid F-4SK in the H form, which is an analog of the perfluorinated resinsulfonic acid Nafion-H. To compare catalyst activity of the perfluorinated resinsulfonic acid in decomposition of cumene hydroperoxide, CHP was also decomposed in presence of KU-2 resin. It was found that during repeated use over a period of 150 h the activity of KU-2 catalyst under analogous conditions fell by 4-6%. During the same time the activity of the perfluorinated resinsulfonic acid remained unchanged. It is also known that the presence of a strong acid in the reaction mixture causes formation of by-products, namely the products of condensation of phenol with acetone and dimethylphenylcarbinol, and of dehydration of dimethylphenylcarbinol, with formation of alpha -methylstyrene and products of greater complexity.
- Etlis,Beshenova,Semenova,Shomina,Dreiman,Balaev
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p. 551 - 555
(2007/10/02)
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- Halogen-containing esters as pH regulators in textile finishing processes
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Disclosed is a textile finishing process in which there is employed, as pH regulator, a compound or mixture of compounds of formula I, STR1 in which N IS 0 OR 1, P is 0 or an integer from 1 to 6, Q is 2 or 3, X is a halogen, Each of Y and Z, independently, is hydrogen or halogen, and A is hydrogen, phenyl, C1-12 alkyl, or a radical of formula (a), (b) or (c), STR2 WHERE R IS 1 TO 4, S is 0 or an integer from 1 to 4, X, y z and n are as defined above, With the proviso that p is other than 0 when A is hydrogen or a radical of formula (c).
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